1. Field of the Invention
The present invention relates to a phosphonium salt compound having an acryl group, which is a raw material for producing a cationic polymer and is useful as an antistatic agent, an antibacterial agent and the like.
2. Discussion of the Background
A phosphonium salt compound having an acryl group is useful as a raw material for producing a cationic polymer. Unlike a quaternary ammonium salt which is also a cationic compound, the monomer and polymer of the phosphonium salt compound having an acryl group has excellent heat resistance and chemical stability due to firm P--C bond, and recently their potential uses and applications in many fields have been actively examined. For example, a polymeric immobilized antibacterial agent (Japanese Patent Laid-Open No. 7-25714), antibacterial inorganic powder (Japanese Patent Laid-Open No. 7-145014), and antibacterial sol (Japanese Patent Laid-Open No. 7-187928) and the like have been disclosed. An antistatic agent that takes advantage of its cationic property have also been proposed.
Such compounds are usually synthesized according to the following reaction formula (A) or (B). ##STR2##
Nevertheless, when a basic catalyst such as pyridine and triethylamine is used for the above-mentioned first reaction (A), the product must be purified and separated from the catalyst by distillation. Therefore, the yield becomes inferior and the procedure is also very complicated. Moreover, when the alkylene chain is lengthened, the boiling point of the product is increased, which restricts the compounds from being synthesized.
Further, in the second reaction (B) wherein the above-mentioned halide having the acryl group is allowed to react with the triorganophosphine, elevated reaction temperatures and long reaction times are required. In addition, when a compound having a polymerizable functional group is synthesized a polymerization inhibitor is normally added, but a polymerized substance and an unreacted substance tend to be mixed in the obtained product when heating at an elevated temperature for a long period of time, and a product with high purity can not be obtained.
In consideration of the above-mentioned situation, as a result of an extensive study to produce a phosphonium salt having an acryl group with high purity, in a high yields and with a simple procedure, the present inventors have found that the phosphonium salt compound having an acryl group with high purity can be easily obtained by reacting a hydroxyalkyl trialkyl phosphonium halide with an unsaturated aliphatic carboxylic acid halide, and achieved the present invention.
Accordingly, an object of the present invention is to provide an industrially advantageous process for preparing a phosphonium salt having an acryl group which allows for the production of a homopolymer or a copolymer.